JP3964935B2 - 有機フッ素化合物の合成方法 - Google Patents
有機フッ素化合物の合成方法 Download PDFInfo
- Publication number
- JP3964935B2 JP3964935B2 JP50735797A JP50735797A JP3964935B2 JP 3964935 B2 JP3964935 B2 JP 3964935B2 JP 50735797 A JP50735797 A JP 50735797A JP 50735797 A JP50735797 A JP 50735797A JP 3964935 B2 JP3964935 B2 JP 3964935B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- fluorine
- substituents
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000004812 organic fluorine compounds Chemical class 0.000 title description 2
- 238000001308 synthesis method Methods 0.000 title 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 37
- 229910052731 fluorine Inorganic materials 0.000 claims description 37
- 239000011737 fluorine Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- 239000007789 gas Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- 125000001741 organic sulfur group Chemical group 0.000 claims description 5
- 239000002002 slurry Substances 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 4
- 238000003682 fluorination reaction Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 150000002019 disulfides Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007788 liquid Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical class [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 4
- KWVVTSALYXIJSS-UHFFFAOYSA-L silver(ii) fluoride Chemical compound [F-].[F-].[Ag+2] KWVVTSALYXIJSS-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- -1 aryl disulfides Chemical class 0.000 description 3
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 2
- KWGZRLZJBLEVFZ-UHFFFAOYSA-N 1-nitro-4-[(4-nitrophenyl)disulfanyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1SSC1=CC=C([N+]([O-])=O)C=C1 KWGZRLZJBLEVFZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229940096017 silver fluoride Drugs 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- CENMEFBGLSDHKN-UHFFFAOYSA-N 1-methylsulfanyl-4-nitrobenzene Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)SC.[N+](=O)([O-])C1=CC=C(C=C1)SC CENMEFBGLSDHKN-UHFFFAOYSA-N 0.000 description 1
- ODOFDWDUSSFUMN-UHFFFAOYSA-N 1-nitro-3-[(3-nitrophenyl)disulfanyl]benzene Chemical compound [O-][N+](=O)C1=CC=CC(SSC=2C=C(C=CC=2)[N+]([O-])=O)=C1 ODOFDWDUSSFUMN-UHFFFAOYSA-N 0.000 description 1
- WCMLRSZJUIKVCW-UHFFFAOYSA-N 4-(trifluoromethyl)benzenethiol Chemical compound FC(F)(F)C1=CC=C(S)C=C1 WCMLRSZJUIKVCW-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- BQNPYLXJOMKHIP-UHFFFAOYSA-N 4-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1.[O-][N+](=O)C1=CC=C(S)C=C1 BQNPYLXJOMKHIP-UHFFFAOYSA-N 0.000 description 1
- JBGHTSSFSSUKLR-UHFFFAOYSA-N 4-nitrophenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 JBGHTSSFSSUKLR-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 229910021608 Silver(I) fluoride Inorganic materials 0.000 description 1
- QFCATAXIBQZXRC-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1)SSC1=C(C=CC=C1)[N+](=O)[O-].[N+](=O)([O-])C1=C(C=CC=C1)S(F)(F)F Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)SSC1=C(C=CC=C1)[N+](=O)[O-].[N+](=O)([O-])C1=C(C=CC=C1)S(F)(F)F QFCATAXIBQZXRC-UHFFFAOYSA-N 0.000 description 1
- DQEBOCAGRCHGEP-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)SSC1=CC=C(C=C1)[N+](=O)[O-].C(Cl)(Cl)Cl Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)SSC1=CC=C(C=C1)[N+](=O)[O-].C(Cl)(Cl)Cl DQEBOCAGRCHGEP-UHFFFAOYSA-N 0.000 description 1
- JZRBEDSITYUJLC-UHFFFAOYSA-N acetonitrile 1-nitro-4-[(4-nitrophenyl)disulfanyl]benzene Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)SSC1=CC=C(C=C1)[N+](=O)[O-].C(C)#N JZRBEDSITYUJLC-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
- AGOVKHDXZGCCCN-UHFFFAOYSA-N trifluoro-(2-nitrophenyl)-$l^{4}-sulfane Chemical compound [O-][N+](=O)C1=CC=CC=C1S(F)(F)F AGOVKHDXZGCCCN-UHFFFAOYSA-N 0.000 description 1
- QEYZGWCLGPZISU-UHFFFAOYSA-N trifluoro-(4-nitrophenyl)-$l^{4}-sulfane Chemical compound [O-][N+](=O)C1=CC=C(S(F)(F)F)C=C1 QEYZGWCLGPZISU-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9515599.0A GB9515599D0 (en) | 1995-07-29 | 1995-07-29 | The preparation of fluorinated organic compounds |
| GB9515599.0 | 1995-07-29 | ||
| PCT/GB1996/001829 WO1997005106A1 (en) | 1995-07-29 | 1996-07-26 | The preparation of fluorinated organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10507206A JPH10507206A (ja) | 1998-07-14 |
| JP3964935B2 true JP3964935B2 (ja) | 2007-08-22 |
Family
ID=10778485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50735797A Expired - Fee Related JP3964935B2 (ja) | 1995-07-29 | 1996-07-26 | 有機フッ素化合物の合成方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5741935A (zh) |
| EP (1) | EP0784614B1 (zh) |
| JP (1) | JP3964935B2 (zh) |
| KR (1) | KR100448730B1 (zh) |
| CN (1) | CN1084733C (zh) |
| AU (1) | AU6745696A (zh) |
| CA (1) | CA2200734C (zh) |
| DE (1) | DE69604560T2 (zh) |
| ES (1) | ES2140119T3 (zh) |
| GB (1) | GB9515599D0 (zh) |
| NO (1) | NO971412L (zh) |
| RU (1) | RU2166498C2 (zh) |
| WO (1) | WO1997005106A1 (zh) |
| ZA (1) | ZA966427B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112015005812B4 (de) | 2014-12-25 | 2018-12-27 | Ube Industries, Ltd. | Verfahren zur Herstellung einer stickstoffhaltigen Pentafluorsulfanylbenzol-Verbindung |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9606015D0 (en) * | 1996-03-22 | 1996-05-22 | Rhone Poulenc Agriculture | New herbicides |
| GB0028797D0 (en) * | 2000-11-25 | 2001-01-10 | F2 Chemicals Ltd | Polyfluorinated derivatives |
| US6919484B2 (en) * | 2002-07-25 | 2005-07-19 | University Of Florida | Method for incorporation of pentafluorosulfanyl (SF5) substituents into aliphatic and aromatic compounds |
| US7015176B2 (en) * | 2003-06-03 | 2006-03-21 | Air Products And Chemicals, Inc. | Process for the synthesis of aryl sulfurpentafluorides |
| US20050124666A1 (en) * | 2003-11-13 | 2005-06-09 | Aventis Pharma Deutschland Gmbh | Pentafluorosulfanylbenzoylguanidines, process for their preparation, use as a medicament or diagnostic aid, and medicament comprising same |
| US7126026B2 (en) | 2003-11-13 | 2006-10-24 | Sanofi-Aventis Deutschland Gmbh | Process for preparing 4-pentafluorosulfanylbenzoylguanidines |
| US7317124B2 (en) * | 2003-11-13 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Ortho-substituted pentafluorosulfanylbenzenes, process for their preparation and their use as valuable synthetic intermediates |
| DE10353205A1 (de) * | 2003-11-13 | 2005-06-16 | Aventis Pharma Deutschland Gmbh | Ortho-substituierte Pentafluorsulfuranyl-Benzole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als wertvolle Synthese-Zwischenstufen |
| US6958415B2 (en) * | 2003-11-14 | 2005-10-25 | Air Products And Chemicals, Inc. | Synthesis of pentafluorosulfuranyl arylenes |
| DE102005023943A1 (de) * | 2005-05-20 | 2006-11-23 | Grünenthal GmbH | Pentafluorsulfanyl-substituierte Verbindung und deren Verwendung zur Herstellung von Arzneimitteln |
| US7265247B1 (en) * | 2006-07-28 | 2007-09-04 | Im&T Research, Inc. | Substituted phenylsulfur trifluoride and other like fluorinating agents |
| US8676349B2 (en) * | 2006-09-15 | 2014-03-18 | Cardiac Pacemakers, Inc. | Mechanism for releasably engaging an implantable medical device for implantation |
| CA2912220C (en) * | 2007-03-23 | 2017-10-03 | Ube Industries, Ltd. | Process for producing arylsulfur pentafluorides |
| US8399720B2 (en) * | 2007-03-23 | 2013-03-19 | Ube Industries, Ltd. | Methods for producing fluorinated phenylsulfur pentafluorides |
| US8030516B2 (en) * | 2007-10-19 | 2011-10-04 | Ube Industries, Ltd. | Methods for producing perfluoroalkanedi(sulfonyl chloride) |
| WO2009076345A1 (en) * | 2007-12-11 | 2009-06-18 | Im & T Research, Inc. | Methods and compositions for producing difluoromethylene-and trifluoromethyl-containing compounds |
| TW201006787A (en) * | 2008-03-07 | 2010-02-16 | Im & T Res Inc | Fluorination processes with arylsulfur halotetrafluorides |
| EP2323974A1 (en) * | 2008-08-18 | 2011-05-25 | Ube Industries, Ltd. | Methods for preparing fluoroalkyl arylsulfinyl compounds and fluorinated compounds thereto |
| JP5574280B2 (ja) * | 2008-09-22 | 2014-08-20 | 宇部興産株式会社 | ポリ（ペンタフルオロスルファニル）芳香族化合物の製造方法 |
| US20100174096A1 (en) * | 2009-01-05 | 2010-07-08 | Im&T Research, Inc. | Methods for Production of Optically Active Fluoropyrrolidine Derivatives |
| WO2010081014A1 (en) | 2009-01-09 | 2010-07-15 | Im&T Research, Inc. | Novel 4-fluoropyrrolidine-2-carbonyl fluoride compounds and their preparative methods |
| CZ303004B6 (cs) | 2010-10-07 | 2012-02-15 | Ústav organické chemie a biochemie Akademie ved CR v.v.i. | Zpusob prípravy substituovaných 3- a 4-(pentafluorsulfanyl)benzenu |
| US9108910B2 (en) | 2011-02-15 | 2015-08-18 | Ube Industries, Ltd. | Industrial methods for producing arylsulfur pentafluorides |
| CA2858157A1 (en) * | 2011-12-06 | 2013-06-13 | Ube Industries, Ltd. | Method for producing pentafluorosulfanyl benzoic acid |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA682749A (en) * | 1964-03-24 | A. Sheppard William | Arylsulfur pentafluorides and preparation | |
| US522070A (en) * | 1894-06-26 | maidhof | ||
| US3117158A (en) * | 1959-03-16 | 1964-01-07 | Du Pont | Aminoarylsulfur pentafluorides |
| US3102903A (en) * | 1961-10-31 | 1963-09-03 | Du Pont | Carbonylic compounds containing the sf5 function |
| GB9307245D0 (en) * | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Process |
-
1995
- 1995-07-29 GB GBGB9515599.0A patent/GB9515599D0/en active Pending
-
1996
- 1996-07-26 CA CA002200734A patent/CA2200734C/en not_active Expired - Fee Related
- 1996-07-26 ES ES96927750T patent/ES2140119T3/es not_active Expired - Lifetime
- 1996-07-26 DE DE69604560T patent/DE69604560T2/de not_active Expired - Lifetime
- 1996-07-26 AU AU67456/96A patent/AU6745696A/en not_active Abandoned
- 1996-07-26 WO PCT/GB1996/001829 patent/WO1997005106A1/en active IP Right Grant
- 1996-07-26 US US08/809,771 patent/US5741935A/en not_active Expired - Lifetime
- 1996-07-26 RU RU97107003/04A patent/RU2166498C2/ru not_active IP Right Cessation
- 1996-07-26 JP JP50735797A patent/JP3964935B2/ja not_active Expired - Fee Related
- 1996-07-26 CN CN96191136A patent/CN1084733C/zh not_active Expired - Fee Related
- 1996-07-26 EP EP96927750A patent/EP0784614B1/en not_active Expired - Lifetime
- 1996-07-26 KR KR1019970701903A patent/KR100448730B1/ko not_active IP Right Cessation
- 1996-07-29 ZA ZA9606427A patent/ZA966427B/xx unknown
-
1997
- 1997-03-25 NO NO971412A patent/NO971412L/no not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE112015005812B4 (de) | 2014-12-25 | 2018-12-27 | Ube Industries, Ltd. | Verfahren zur Herstellung einer stickstoffhaltigen Pentafluorsulfanylbenzol-Verbindung |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9515599D0 (en) | 1995-09-27 |
| RU2166498C2 (ru) | 2001-05-10 |
| CA2200734C (en) | 2008-05-13 |
| KR100448730B1 (ko) | 2004-12-03 |
| US5741935A (en) | 1998-04-21 |
| AU6745696A (en) | 1997-02-26 |
| NO971412D0 (no) | 1997-03-25 |
| WO1997005106A1 (en) | 1997-02-13 |
| DE69604560D1 (de) | 1999-11-11 |
| NO971412L (no) | 1997-03-25 |
| CA2200734A1 (en) | 1997-02-13 |
| CN1165512A (zh) | 1997-11-19 |
| JPH10507206A (ja) | 1998-07-14 |
| CN1084733C (zh) | 2002-05-15 |
| EP0784614A1 (en) | 1997-07-23 |
| EP0784614B1 (en) | 1999-10-06 |
| ES2140119T3 (es) | 2000-02-16 |
| KR970706248A (ko) | 1997-11-03 |
| DE69604560T2 (de) | 2000-05-04 |
| ZA966427B (en) | 1997-02-19 |
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